Beauty 101: "I Fail At Keeping Lipstick On My Mouth"

While we've spent the past two weekends discussing the hair on one's head and the hair, um, everywhere else, today our Beauty 101 series returns to the world of cosmetics, focusing on the lips:

When I asked for suggestions for a Beauty 101 topic, many commenters expressed their frustration with lipstick, and asked for help in several lip-related areas:

i'd like a topic on red lipstick. how to wear it dressy & casual, for different skin tones, etc.

Lips - how to apply lipstick correctly, and more importantly, how the hell does lipliner work?!

Lip liner/lipstick!

People always say "just color in the whole lip with the pencil" but it looks really bad when I do it. And I don't know what they mean when they say "feather" it into the lip.

And my lipstick looks wonky. So I'm stuck with gloss for now. :)

Lipstick! I can make my eyes all purdy, but when I put on lipstick, I look like a little girl who got into her mother's make up.

Also, I love red lipstick, but I can't seem to find anything that works with my skin tone!

I would love some instruction on lipsticks. I wear lipgloss, but the world of lipstick selection/application seems very scary and bewildering.

How to apply/which brand of lipstick to use that won't be completely gone by the time I've had my first cup of coffee.

Lipstick! I suck at lipstick application. My lips aren't as full as I'd like and any color aside from the lightest plays up that thinness. Not only do I not know what colors I should use, but I can't put it on and make it stay or look "normal" - my lips look unevenly shaped. So I just stick with gloss or chapstick (Burt's Bees, which I LOVE). I'd still like to wear (and wear well) lipstick once in awhile!

Lip liner baffles me. I somehow have managed to purchase said item countless times in the vain hope of knowing what the hell it is for, but no dice.

Things I would like to learn: how to find a lip color that is long-lasting (requiring little to no reapplication) that makes it look like I'm not wearing lipstick, but at the same time stops that gross pale way my naked lips look. A natural rosiness, if you will.

Oh! Another thing: Red lipstick. I fail at keeping lipstick on my mouth, I don't even bother with it. How do you wear red lipstick and look like Dita Von Teese instead of a clown?

I'd say my downfall is choosing a lipstick color. I never wear it, and when I do, the colors I choose never look right. I look like some sort of hooker clown, or I look like I'm sick and pale. So I just go back to no lipstick. Someday, though, I'll have to figure it out.

Other questions that seemed to pop up fairly often:

1. How do I get lip color to last?

2. How can I avoid dry/chapped lips?

3. How do I pick the right lip color?

4. What's the difference between stain, stick, and gloss? Can I/should I use more than one at a time?

5. How do I use lip liner properly?

Think you can help? Post your tips in the comments below, or email them to me with "Lipstick" in the subject line by 11pmEST. (I can't use all of your comments or emails, but I appreciate all of them!) A roundup of tips and tricks will be posted tomorrow.